Thoughts on Hiring a Design Leader (director-level and above)

April 2018, I suddenly found myself out of a job—included in a round of layoffs that shut down the office I worked in. As there was no long drawn out descent preceding my being let go, I wasn’t burned out, and, in fact, found myself energized. I dove into the job market, looking for opportunities to channel these energies productively.

After numerous discussions as a candidate, including 4 or 5 day-long onsites with different companies, I came away with the distinct impression that most (nearly all?) do not know how to hire design leaders. And it’s not just me—conversations with many peers suggest that this is a widespread phenomenon. Recent evidence includes this moderately viral Twitter post:

First: Understand What You’re Actually Hiring For

(For this post, I’m focusing on director-level and above roles, including the nebulous “Head of Design.” While much of what follows applies to hiring anyone, there are elements discussed specific to the more senior roles on a design team.)

The foundational issue affecting hiring design leaders that is that the role of design leadership is poorly understood. This is to be expected: for the vast majority of companies, real-deal design leadership is a totally new role. The hiring manager for such a role (often a head of Product Management) has never hired for this role before, has only a vague sense of its importance (as part of a product-engineer-design triumvirate within product development); and there’s no one internally to turn to to get help.

The hiring manager falls back on what they know about design, which is not sophisticated or nuanced. It’s often along the lines of: “Design is the execution of visual interfaces, and so I want my head of design to be good at executing visual interfaces.” Or, “We need a creative visionary to inspire the team to greatness.”

This is probably the single biggest shortcoming I’ve seen in how companies profile design leaders — as creative visionaries with shiny portfolios. What this doesn’t take into account is that design direction is at best a third of a design leader’s role, and often less than 25% of the work they actually do. Most design directors-and-above are:

  • Creative leaders (providing direction for their team in framing and solving problems)
  • Managers (recruiting and hiring designers; growing their designers through 1-on-1s and other professional development practices; conducting difficult conversations with team members who are struggling)
  • Diplomats (engaging cross-functional peers in helping them understand how design works; where design can be most valuable; coordinating practices and processes; advocating for giving ‘space’ for design to be done right)
  • Champions (managing up with stakeholders and executives; serving as a 💩☂️ to protect the team from executive cluelessness and misbehavior; sticking up for good solutions in the face of resistance from senior leadership)
  • Operators (working with internal functions such as HR, finance, and facilities to make sure the team is getting the resources they need to succeed, the compensation they deserve in the marketplace, and the career paths they warrant as they grow)

It often turns out that creative direction is the least important aspect of a design leader’s role, as that can be delegated to capable design managers or senior designers, whereas the management, diplomatic, champion, and operator activities are the ones truly specific to the leader.

And so when a company hiring a design leader insists on seeing a portfolio before having a conversation, or decides not to hire someone because, regardless of their organizational aptitude, their prior work doesn’t appear “inspirational,” it’s a symptom of how the company simply doesn’t appreciate the work that needs to get done.

What’s most disappointing is how hiring managers who should know better fall into these traps. Recently I had a VP of Product, who was ex-IDEO, tell me that: “I’m looking for someone with a longer track record at consumer product companies.” It’s hard to know what to make of a statement like that, because it suggests that it doesn’t matter that the person has built and lead successful design organizations in multiple contexts. By calling out “consumer product,” this VP of Product seems to think that the head of design will be hands on in directing the work day-to-day, responsible for the look-and-feel, and that their team exists to execute on their direction. This is not at all how design actually happens.

Second: Run your recruiting processes right

Looking past the fact that many/most companies don’t really know what they want in a design leader, the mechanics by which they then recruit and hire them are also poorly managed.

The Catch-22: Hiring a design leader without a design leader

Most companies approach hiring a design leader like they do any other role—as a joint effort between a hiring manager and a recruiter. However, the hiring manager often doesn’t understand the role (as described above), and the recruiter is primarily there to manage the process. The duo stumbles ahead, resigned to their cluelessness. This doesn’t have to be. Finding the right design leader is too important to conduct in a haphazard way. If you don’t have someone internal you can turn to, then bring on an external consultant to help manage the process.

By which I don’t mean to simply rely on an external recruiter. Recruiters can be helpful in sourcing and doing an initial vetting of candidates. But, for director-level-and-above roles, most leadership recruiters are new to design, and don’t understand the idiosyncratic particularities of what the role entails. And there is a dearth of design-focused leadership recruiting who really gets it.

Instead, seek consultants, preferably folks with recent experience running in-house teams, to provide guidance through the process.

Conducting hiring interviews responsibly

A cursory Googling reveals that practice and process of hiring interviews are a mess. This is particularly problematic because these interviews end up being the leading factor in making a hiring decision. It is possible to run a useful hiring interview process. Some (non-exhaustive) guidance:

Use phone screens judiciously. Bringing someone on site for a day of interviews is a big investment for everyone —the candidate and the interviewers. Make sure it’s worth the time by conducting solid phone screens. The whole point of the phone screens is to qualify the candidate (and for the candidate to qualify the company) to determine if it’s worth everyone’s time to bring this person on-site.

Conduct 2 screens. The first screen is done by the hiring manager (or the external consultant supporting the team) and ensures that the candidate understands the role, appears to meet the basic requirements across the role (such as the 5 elements listed in the role definition section earlier), and demonstrates strong communications skills through how they articulate their experience. If the candidate passes the first screen, then a second screen (performed by either a peer leader or a senior person on the team to be joined) digs deeper into the candidates skill set to evaluate whether this person is suitable for the role. The second screen also simply provides an alternate perspective before making the commitment to bring someone in.

Structure a cross-functional, range-of-experience on-site interview day, including a portfolio presentation, but try to keep it to no more than 5 conversations… AND NO DESIGN EXERCISES. During their on-site, a design leader should meet 4 or 5 people, representing a cross-section of folks they would work with — including their hiring manager, someone who would report to them, a functional peer, and a cross-functional peer (e.g, a product manager or engineer). The day begins with the candidate presenting their work history (kind of like a portfolio, but less about ‘stuff they’ve designed,’ than key work experiences they’ve had) to the entire hiring panel, so that it doesn’t have to be repeated in each separate interview. 

Avoid exhaustive interview practices. Interview panels see diminishing returns once you get past 5 interviewers, and it’s important to be mindful of the time investment being made.

Give each interviewer a specific and distinct area to address. A common failing of interview days is that there is no coordination across interviewers, and so folks just ask whatever they’re interested in. The goal is to paint a complete picture of the candidate, which is why the panel represents a set of different relationships. Make sure each interviewer knows what they’re expected to focus on.

Make sure a direct report is on the interview panel. I have been stunned by the number of times I’ve interviewed for a managment position and no one who would be reporting to me was involved in the process. It’s shameful, and sends a miserable signal to the team that their views are not worth considering.

And this should go without saying, but the example from the Twitter post above suggests, sadly, otherwise: no design exercises. I’ve written at length about why they make bad interviewing practice.

Be explicit about what you’re looking for ahead of time. The judgments made about a candidate during an interview should not be arbitrary. There should be a clear understanding of the criteria under consideration, what you’re looking for, and an instrument that enables a fair assessment of the candidate against those criteria.

Be empathetic and recognize a range of communication styles. For many candidates (including myself!) interviews are stressful situations. You’re being grilled. You feel like you’re being judged. You want to demonstrate your capability. The anxiety ahead of time may have affected your sleep. Given these situations, candidates are not often their best selves. For me personally, I get in my head, over-excited about the subject at hand, and come on too strong. Others may trip over their words, not look you in the eye, fidget, etc. This is why it’s so crucial to have articulated a set of criteria to gauge success (point 3)–you have to be mindful of the potential impact of personality to inadvertently sway a decision.

Balance what transpired in the interview with thorough reference checks. For all the folly that transpires during the recruiting process, none perplexes me more than how few companies routinely conduct reference checks. Who better to know how someone performs and behaves in the workplace than people who have worked with that person? That companies will give more weight to a series of 45 minute interview conversations with what are essentially strangers, than someone’s actual coworker experience is mind-boggling. I have directly felt this pain, as more than once after an interview process, I was told that they were not going to go forward because I came across as domineering. I grant that I come on strong in those situations (as explained before). I also know that in every internal 360 review I’ve been part of, my communication style has never been an issue. And I don’t want to make this about me — I’m using my story as a case in point, and know that countless others have had similarly troublesome experiences.

That’s not all, but it’s enough for now

There’s plenty more than goes into successful recruiting and hiring — writing a job description and placing it well; sourcing candidates; pulling together a strong offer. Recruiting and hiring is a bear to contend with (detailing the process was the single longest chapter in our book), and most companies just don’t appreciate what it takes to do it right.

For those that are looking to hire design leaders—what are the biggest challenges you’re facing? Please let us know in the comments below. 

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